Annual Events & Festivals

Browse our listing of annual events and make your plans! From historic downtown Brooksville to area parks and the sparkling Gulf of Mexico coast, many events celebrate our pleasant Florida weather. Pick from a brimming buffet of culinary celebrations. Step back in time with historical re-enactments and watch demonstrations of other cultures and lifestyles. Explore your interests. Discover unique entertainment. Dance, shop, taste, look and listen throughout an eventful year here in Nature’s Place to Play.


January 1, 2022

Croom Zoom 100K, 50K & 25K

The Croom Zoom 100K/50K/25K courses uses the extensive trails of Croom Park. The trails wind through oak hammocks on a well-defined trail that takes runners through some of the best cross-country running terrain in Florida. Tucker Hill Fire Tower Parking Lot, 26416 Croom Rd., Brooksville.

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January 2, 2022

Spring Hill Marathon Mania / Hand Cyclists Marathon

Marathon, Half-Marathon, 10K or 5K – this Boston Marathon Qualifier is Central Florida’s first marathon race of the year. Anderson Snow Park, 1360 Anderson Snow Rd., Spring Hill.

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January 6-10 & 12-16, 2022

Florida Gulf Coast Cluster AKC All-Breed Dog Show

Ten days of competitions featuring ten American Kennel Club All-Breed Dog Shows, two days of specialty shows, Conformation, Junior Showmanship, Obedience and Rally Trials, plus visits with the dogs and their handlers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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February 4-5, 2022

Celtic Family Jamboree

A unique family-friendly Celtic experience sharing tradition through live performance, workshops and crafts. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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Postponed to 2022

Tin Can Tourists Winter Convention Open House

Tin Can Tourists celebrate the preservation of classic Gulfstream camping trailers and motor coaches dating from the 1940’s to the 1960’s. The TCT Open House is from 11am – 3pm. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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February 5-6, 2022

Brooksville Native American Festival

The family-friendly festival features authentic dancing and music, artists and craftsmen from around the country, primitive skills demonstrations, and Native foods like fry bread and buffalo burgers. Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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February 2021

Heritage Day

A celebration of 1800’s Hernando County, including historic home tours, carriage rides, museum tours, crafts and heritage activities for all ages. May-Stringer Historical Museum, 601 Museum Court, Brooksville.

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February 24-26, 2022

Florida Classic Music Fest

Enjoy three days of live Bluegrass, Classic Country, Oldies, Cajun/Zydeco and more! Florida Classic Park, 5360 Lockhart Rd., Brooksville.

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February 13, 2021

Good Neighbor Trail 5K

Come join the fun on one of Brooksville’s finest paved trails shaded with old oak trees and beautiful scenery. Race begins at the corner of Weatherly Rd & Richbarn Rd., Brooksville.

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March 4-6, 2022

Weeki Wachee Swamp Fest

One of the premier fine arts, crafts and music festivals in the southeast includes the Swamp Monster contest and over 140 vendors and crafters, entertainment, live bands including country, folk, and toe-tapping get-up-and-dance tunes. Linda Pedersen Park, 6300 Shoal Line Blvd., Weeki Wachee.

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March 18-20, 2022

Blues Bash at The Ranch

Enjoy Hot Blues – Cool Nights at this new 3-day music festival. Music, workshops, family and dog-friendly. Choose to camp or buy a day pass at Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 20, 2021

Hernando Bar 5K 10K

This Annual Run is comprised of five year age groups, three deep, plus Master’s Division and Overall Winners and Fastest Lawyer. Weekiwachee Preserve 2345 Osowaw Boulevard, Spring Hill

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March 11-13, 2022

The Will McLean Music Festival

Named for the Father of Florida Folk Music, this festival features entertainment by Florida’s singers and songwriters, including workshops, arts, crafts, poetry reading, storytelling, and children’s activities. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 24-26, 2022

EMS Spring Bluegrass Fest

Enjoy three days of the best in Bluegrass music, stage shows, open mic, workshops, movies, children’s activities, and a Sunday morning Gospel Sing. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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March 20-21, 2021

Central Florida Sportsman’s Expo

Calling all outdoor enthusiasts. From fishing to boating, kayaking, ATVing and RVing, celebrate the outdoor adventurous lifestyle at the inaugural Central Florida Sportsman’s Expo. Tour vendors, view demonstrations and much more at Brooksville’s beautiful Tom Varn Park.

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March 12-13, 2022

Art in the Park: Art, Crafts & Music Festival

The Gulf Coast’s largest Art Festival with over 115 artisans participating in the annual juried show featuring fine art, fine craft, craft artist vendors, student art, and live entertainment. Tom Varn Park, 306 Darby Ln., Brooksville.

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March 2022 – TBA

Florida Agriculture & Wildlife Expo

A showcase of Hernando County’s finest agriculture, wildlife, arts, talent, and industry, plus crafts and entertainment. Brooksville-Tampa Bay Regional Airport, Runway Drive entrance (off US-41 S), Brooksville.

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April 7-9, 2022

Stringbreak Music Festival

This multi-stage Americana music fest features Roots Rock, Alternative Country, Newgrass and Bluegrass. Camping, vendors, and well-planned activities make for a great weekend. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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April 9-17, 2021

Hernando County Fair

You know it’s Spring when the Fair is here! The whole family will enjoy exhibits, Midway rides, games, livestock shows, vendors, food and live entertainment, including evening shows. Hernando County Fairgrounds, 6436 Broad St. (US-41S), Brooksville.

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Postponed to 2022

Brooksville Blueberry Festival

All things blueberry take over historic downtown Brooksville the last weekend of April each year. Filled with family friendly fun, music and food, it’s known as the Best Little Festival in Florida. Historic downtown Brooksville.

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April 3, 2021

Croom 50M/50K/16M Fools Trail Run

The beautiful and challenging 50-mile course follows three repeat loops on the Croom Hiking Trail, through central Florida’s long leaf pines and scrub oak covered hills, past creek bottoms and cypress ponds. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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Weekends in May

Sunflower Maze, Spring Crops and Farm Activities

Maze your way through the paths of 8 to 10-foot-tall sunflowers in search of the exit. Six acres of fun, including hay rides, picnic area, family activities and spring produce. Sweetfields Farm, 17250 Benes Roush Rd., Masaryktown.

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May 13-16, 2021

Orange Blossom Jamboree

This family-friendly music festival features an outdoor pavilion and three stages for continuous entertainment with more than 60 bands. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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May 29, 2021

Spring Lake Memorial Classic

The annual run and walk wind through scenic terrain, including a nature trail through the woods, a horse barn and up and down some challenging hills! The ARC Nature Coast, 5283 Neff Lake Rd., Brooksville.

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First Saturday in July

Scallop Season Opens

Grab your snorkel gear and Diver-down flag and head for the water! The much-anticipated annual scallop season opens and runs into September. Bayport Park, 4140 Cortez Blvd., Brooksville or Hernando Beach Boat Ramp, 4483 Calienta St., Hernando Beach.

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August 13-15, 2021

The Spirit of Woodstock Music Festival

Set in the rolling hills of Brooksville’s Sertoma Youth Ranch, Spirit of Woodstock Music Festival is a camping optional experience you don’t want to miss. With over 80 acres of oak trees, a creek and lake, the picturesque setting is ideal for this family – and pet-friendly – event. Camp or buy single day tickets.

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August 21, 2021

Moon Over Croom – 21M, 14M, 7M Trail Run

Experience Croom like you never have before; running in the dark. The main day-run trail is a well-marked 7-mile loop; glow sticks will mark the course for night. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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August 28-29, 2021

Olive Grove Mill Party Weekend

Tour the orchard, sample fresh oil and olive products, and see the mill that produces Fresh Extra Virgin Olive Oil.  Enjoy workshops, food, beverages, live entertainment and more! The Olive Grove, 15016 Rester Dr., Brooksville.

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October 5, 2021

Papa Joe’s Annual Pasta Fest

Bring your appetite to the 99¢ All-You-Can-Eat pasta event with children’s activities and entertainment. Papa Joe’s Italian Restaurant, 6244 Spring Lake Hwy., Brooksville.

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October 9, 2021

John Holmes 50K, 16M, 9M Trail Run

The John Holmes is the Grand Daddy of 50Ks being the oldest trail run in Florida. This is a classic loop course with 7 mile loops. A beautiful course that winds through the oak and scrub forest of Croom – a must for anyone looking to try a 50K. Tucker Hill Fire Tower Lot, 26416 Croom Rd., Brooksville.

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October 22-23 & 29-30, 2021

Halloween Haunted House

Enjoy spooky hauntings and a fun-filled evening of children’s games, face painting, story-telling, roasting marshmallows around the bonfire, and more! May-Stringer House Historical Museum, 601 Museum Court, Brooksville.

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Weekends in October

Fall RoundUp Farm Fun

Enjoy mazes, hayrides, entertainment, family activities, storytelling, games, produce barn and more. Sweetfields Farm, 7250 Benes Roush Rd., Masaryktown.

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October 9-16, 2021

Founders’ Week Celebration

Celebrating the 164th anniversary of the founding of Brooksville, the entire family will enjoy a variety of events throughout the week. Throughout Historic Brooksville, 20 N. Main Street Area, Brooksville.

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TBA – October 2021

Rocky Horror Picture Show with Live Cast at the Olive Grove Fall Harvest Festival

Enjoy a meatloaf dinner and an interactive performance of  “The Rocky Horror Picture Show.” Costumes welcome! The Olive Grove, 15016 Rester Dr., Brooksville.

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Weekends in October

Fall Corn Maze and Farm Activities

Enjoy the corn and other mazes, hayrides, entertainment, family activities and more. Harvest Moon Farm, 15990 Stur St., Masaryktown.

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October 15-17, 2021

Camping with the Blues

Enjoy three days and three nights of “Blues Under the Stars With The Stars Of The Blues.” Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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October 17, 2020

Mud Endeavor, Castle Canyon

Make some new friends, achieve some new goals and create new memories! This premium course resides on over 100 acres of untouched valleys with unbeaten trails and breathtaking cliffs. Castle Canyon is the site of a rock mining operation that took place in the 1920’s. 10444 Beggs Lane, Brooksville

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November 11-14, 2021

Riverhawk Music Festival

Four days of incredible music and entertainment, workshops and jam sessions. The eclectic array of music, includes Americana, Bluegrass, Jamgrass, Celtic, Newgrass, Cajun and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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November 29-December 13, 2021

Festival of Trees

A beautiful collection of decorated Christmas trees created by local businesses and organizations in the City of Brooksville. Open to the public for viewing and silent auction to bid on decorated trees.

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November 20-21, 2021

Field of Dreams Car Show

The show features street rods, rat rods, classics, four-wheel drives, modern muscle, performance vehicles and more. Plus, visit the Car Corral, swap meet, arts and crafts vendors and enjoy great food and live entertainment. Florida Classic Park, 5360 Lockhart Road, Brooksville.

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November 2020

Taste of the Fields

A fabulous feast, from appetizers to desserts, prepared from local harvests by local chefs; served on the picturesque lawn of historic Chinsegut Hill. Chinsegut Hill Retreat, 22495 Chinsegut Hill Rd., Brooksville.

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November 25-27, 2021

Thanksgiving Bluegrass Festival

Enjoy Thanksgiving dinner, camping, bluegrass and more. Sertoma Youth Ranch, 85 Myers Rd., Brooksville.

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December 2, 2021

Downtown Brooksville’s Christmas Tree Lighting and Christmas on Main Street

Named a Southeast Tourism Society “STS Top 20 Event,” the Brooksville Main Street organization proudly presents the dazzling Christmas tree lighting event at 20 North Main Street in historic downtown Brooksville. Join attendees from around the region to hear live music, shop and eat downtown among the festive scenery.

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December 2021 – TBA

Holiday Season Carriage Rides

During four holiday evenings, enjoy traditional carriage rides around historic downtown Brooksville. View festive shops and decorations, including the spectacular 30 foot courthouse Christmas tree.  20 N. Main St., Brooksville. Reservations required.

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December 4 and 11, 2021

Downton Abbey Christmas

Downton Abbey comes to life on Florida’s Adventure Coast where Lady Grantham will learn there is never a dull moment on a weekend in Brooksville! The Tilted Teacup Tea Room & Boutique, 103 S. Saxon Ave., Brooksville.

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December 16, 2021

Chamber Golf Classic

Join the Annual Chamber Golf Classic at Southern Hills Plantation. 4200 Summit View Drive, Brooksville.

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December 2020

May-Stringer House Night of Lights Tour

Tour this Victorian Mansion after dark, festively lit for teh holiday season. Historic Brooksville, 601 Museum Court, Brooksville.

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December 11, 2021

Kiwanis Christmas Parade

One of the largest and most colorful holiday parades in Florida kicks off at 10am, followed by special activities and shopping in the historic downtown. Historic Brooksville, 20 N. Main St., Brooksville.

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December 4, 2021

Hilly Hundred

Join this large group of cycling enthusiasts on a challenging, invigorating group ride through Florida’s Adventure Coast’s scenic countryside. Organized by Crank Works Bicycles, this is a free (self-supported) ride with voluntary donations encouraged for different local charities.

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